Nicotinoyl chloride → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3-pyridylcarbonyl)thiourea

HRID 721926Notes

Reaction equation

HRID 721926 reaction equation
N1C=CC=C(C(Cl)=O)C=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][CH:16]=[C:15]2[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([N:40]=[C:41]=[S:42])=[O:39])[CH:33]=1>C1(C)C=CC=CC=1.C(O)C>[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([N:40]=[C:41]=[S:42])=[O:39])[CH:33]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][CH:16]=[C:15]2[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:41]([NH:40][C:38]([C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)=[O:39])=[S:42])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 82604Nicotinoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21891030HCID 21891030, compound

Product 2

HCID 21890228N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3-pyridylcarbonyl)thioureaYield 64%HCID 21891030HCID 21891030, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3-Pyridinecarbonyl isothiocyanate was prepared using commercially available 3-pyridinecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3-pyridinecarbonyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (83 mg, yield 64%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-14c84713d7d14f0e9a92172c872e1c98
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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